Methyl Linolenate

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  • Identifiers

    CAS number
    301-00-8

    Molecular formula
    C19H32O2

    SMILES
    CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC

    Safety labels

    Irritant
    Irritant

    Environmental Hazard
    Environmental

    Retention indicies (RI)

    • DB5: 2089.0

  • Odor profile

    Fatty 80.65%
    Oily 63.2%
    Fruity 48.55%
    Waxy 43.4%
    Green 29.77%
    Citrus 27.73%
    Fishy 26.98%
    Pear 26.06%
    Herbal 25.96%
    Sweet 24.59%

    Scent© AI

  • Properties

    XLogP3-AA
    6.2

    Molecular weight
    292.5 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    329°C

    Flash point est.
    178.51 ˚C

  • Synonyms

    • METHYL LINOLENATE
    • 301-00-8
    • methyl (9Z,12Z,15Z)-octadeca-9,12,15-trienoate
    • Methyl alpha-linolenate
    • Linolenic acid, methyl ester
    • Linolenic acid methyl ester
    • Methyl all-cis-9,12,15-octadecatrienoate
    • alpha-Linolenic acid methyl ester
    • Methyl .alpha.-linolenate
    • 9,12,15-Octadecatrienoic acid, methyl ester, (Z,Z,Z)-
    • UNII-0S1NS923K6
    • DTXSID5041560
    • 0S1NS923K6
    • EINECS 206-102-3
    • Methyl cis,cis,cis-octadec-9,12,15-trienoate
    • Linolenic acid-methyl ester
    • NSC 607759
    • NSC-607759
    • Methyl linolenate, .alpha.
    • Methyl (9Z,12Z,15Z)-9,12,15-octadecatrienoate
    • AI3-26935
    • DTXCID3021560
    • CHEBI:133634
    • METHYL LINOLENATE [USP-RS]
    • MFCD00135851
    • cis,cis,cis-9,12,15-Octadecatrienoic acid, methyl ester
    • (Z,Z,Z)-9,12,15-OCTADECATRIENOIC ACID METHYL ESTER
    • methyl (9Z,12Z,15Z)-octadecatrienoate
    • .ALPHA.-LINOLENIC ACID METHYL ESTER
    • FEMA NO. 3411, METHYL LINOLENATE-
    • 9Z,12Z,15Z-Octadecatrienoic acid methyl ester
    • [Z,Z,Z]-9,12,15-Octadecadienoic acid methyl ester
    • (Z,Z,Z)-9,12,15-Octadecatrienoic acid, methyl ester
    • Linolenic acid-methyl ester 10 microg/mL in Acetonitrile
    • METHYL CIS,CIS,CIS-OCTADECA-9,12,15-TRIENOATE
    • METHYL LINOLENATE (USP-RS)
    • (Z,Z,Z)-9,12,15-Octadecadienoate methyl ester
    • [Z,Z,Z]-9,12,15-Octadecadienoate methyl ester
    • (Z,Z,Z)-9,12,15-Octadecadienoic acid methyl ester
    • Methyl a-linolenate
    • Methyl cis,cis,cis-9,12,15-octadecatrienoate
    • Methyl I+--linolenate
    • Methyl a-linolenic acid
    • Linolenate, methyl ester
    • Methyl linolenate, alpha
    • a-Linolenate methyl ester
    • Methyl I+--linolenic acid
    • Methyl alpha-linolenic acid
    • Methyl linolenate (Standard)
    • SCHEMBL55951
    • alpha-Linolenate methyl ester
    • a-Linolenic acid methyl ester
    • Methyl linolenate, tech grade
    • CHEMBL1172198
    • MSK1854
    • Methyl linolenate, >=99% (GC)
    • (9Z,12Z,15Z)-Methyl linolenate
    • Methyl linolenate, (Z,Z,Z)-isomer
    • Tox21_303764
    • HY-21268R
    • NSC607759
    • Methyl linolenate, analytical standard
    • AKOS030526132
    • CS-5627
    • FM66586
    • NCGC00357264-01
    • AC-33780
    • AS-56871
    • CAS-301-00-8
    • DA-75479
    • HY-21268
    • L0051
    • Methyl (9Z,12Z,15Z)-octadecatrienoic acid
    • NS00012941
    • S0324
    • Methyl linolenate, technical, 70-80% (GC)
    • D91234
    • Methyl all-cis-9,12,15-octadecatrienoic acid
    • A912782
    • 0FE5A6DF-F28B-4F68-A34B-F46CBC4F91AD
    • Methyl cis,cis,cis-octadec-9,12,15-trienoic acid
    • cis,cis,cis-9,12,15-Octadecatrienoate, methyl ester
    • Methyl (9Z,12Z,15Z)-9,12,15-octadecatrienoate #
    • Q27237155
    • cis-9,cis-12,cis-15 Octadecadienoic acid methyl ester
    • Methyl (9Z,12Z,15Z)-9,12,15-octadecatrienoic acid
    • Octadecatrienoic acid methylester, 9,12,15-(Z,Z,Z)-
    • cis,cis,cis-octadeca-9,12,15-trienoic acid methyl ester
    • Methyl linolenate, United States Pharmacopeia (USP) Reference Standard
    • 805-333-2

  • Applications

    Methyl linolenate (CAS 301-00-8) is the methyl ester of α-linolenic acid (C18:3) and is widely used as a FAME analytical standard in GC/GC-MS to profile fatty acids in vegetable oils and fats for quality control, and as a model substrate to study autoxidation, lipid peroxidation, oxidative stability, and antioxidant inhibition mechanisms; in catalysis and biocatalysis it is employed to probe lipase selectivity, transesterification, hydrolysis, and as a precursor to recover ALA; in materials and energy it serves as a bio-based feedstock for biodiesel research (assessing impacts on cetane number, cold-flow, and NOx) and can be epoxidized/oligomerized to yield bio-plasticizers, PVC stabilizers, green solvents, reactive diluents, and UV/alkyd coatings; it is also a starting point for double-bond cleavage (ozonolysis, metathesis) to specialty monomers and diacids, and an intermediate toward surfactants and biodegradable lubricant additives; because it is highly prone to oxidation, it should be stored airtight under inert gas, protected from light and heat, typically with antioxidants; common sources include flaxseed, soybean, and algal oils.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 195.92
    methanol 172.83
    isopropanol 170.01
    water 0.01
    ethyl acetate 567.68
    n-propanol 193.9
    acetone 426.46
    n-butanol 226.75
    acetonitrile 145.05
    DMF 368.19
    toluene 229.56
    isobutanol 155.67
    1,4-dioxane 676.96
    methyl acetate 289.57
    THF 1235.0
    2-butanone 495.89
    n-pentanol 198.17
    sec-butanol 223.14
    n-hexane 54.94
    ethylene glycol 6.88
    NMP 511.01
    cyclohexane 207.67
    DMSO 657.71
    n-butyl acetate 432.33
    n-octanol 82.53
    chloroform 1172.74
    n-propyl acetate 532.7
    acetic acid 130.36
    dichloromethane 1417.15
    cyclohexanone 982.88
    propylene glycol 27.65
    isopropyl acetate 418.01
    DMAc 635.53
    2-ethoxyethanol 334.47
    isopentanol 246.34
    n-heptane 35.56
    ethyl formate 173.97
    1,2-dichloroethane 1023.36
    n-hexanol 156.76
    2-methoxyethanol 327.14
    isobutyl acetate 300.25
    tetrachloromethane 188.99
    n-pentyl acetate 367.26
    transcutol 1722.58
    n-heptanol 89.77
    ethylbenzene 154.74
    MIBK 389.82
    2-propoxyethanol 312.08
    tert-butanol 283.96
    MTBE 498.94
    2-butoxyethanol 228.84
    propionic acid 118.59
    o-xylene 162.28
    formic acid 21.96
    diethyl ether 608.35
    m-xylene 158.69
    p-xylene 186.39
    chlorobenzene 306.46
    dimethyl carbonate 80.65
    n-octane 14.35
    formamide 49.24
    cyclopentanone 793.43
    2-pentanone 555.27
    anisole 328.21
    cyclopentyl methyl ether 647.61
    gamma-butyrolactone 613.98
    1-methoxy-2-propanol 314.11
    pyridine 565.71
    3-pentanone 389.45
    furfural 461.63
    n-dodecane 9.08
    diethylene glycol 108.19
    diisopropyl ether 156.17
    tert-amyl alcohol 298.28
    acetylacetone 535.31
    n-hexadecane 11.1
    acetophenone 326.83
    methyl propionate 305.88
    isopentyl acetate 402.81
    trichloroethylene 1402.68
    n-nonanol 84.52
    cyclohexanol 312.85
    benzyl alcohol 186.05
    2-ethylhexanol 140.32
    isooctanol 96.68
    dipropyl ether 320.58
    1,2-dichlorobenzene 324.65
    ethyl lactate 129.12
    propylene carbonate 323.93
    n-methylformamide 111.97
    2-pentanol 188.51
    n-pentane 37.05
    1-propoxy-2-propanol 287.02
    1-methoxy-2-propyl acetate 407.62
    2-(2-methoxypropoxy) propanol 252.69
    mesitylene 111.84
    ε-caprolactone 701.63
    p-cymene 87.51
    epichlorohydrin 1040.21
    1,1,1-trichloroethane 753.74
    2-aminoethanol 37.43
    morpholine-4-carbaldehyde 498.7
    sulfolane 816.69
    2,2,4-trimethylpentane 31.35
    2-methyltetrahydrofuran 959.55
    n-hexyl acetate 359.66
    isooctane 20.37
    2-(2-butoxyethoxy)ethanol 372.18
    sec-butyl acetate 369.94
    tert-butyl acetate 502.12
    decalin 67.05
    glycerin 40.72
    diglyme 849.32
    acrylic acid 70.62
    isopropyl myristate 123.55
    n-butyric acid 340.68
    acetyl acetate 258.18
    di(2-ethylhexyl) phthalate 100.11
    ethyl propionate 413.58
    nitromethane 313.76
    1,2-diethoxyethane 684.18
    benzonitrile 235.58
    trioctyl phosphate 68.3
    1-bromopropane 635.92
    gamma-valerolactone 928.79
    n-decanol 57.27
    triethyl phosphate 162.73
    4-methyl-2-pentanol 115.47
    propionitrile 185.5
    vinylene carbonate 244.16
    1,1,2-trichlorotrifluoroethane 473.63
    DMS 205.5
    cumene 100.86
    2-octanol 71.74
    2-hexanone 479.59
    octyl acetate 144.38
    limonene 170.96
    1,2-dimethoxyethane 780.96
    ethyl orthosilicate 174.47
    tributyl phosphate 99.08
    diacetone alcohol 393.58
    N,N-dimethylaniline 213.65
    acrylonitrile 157.55
    aniline 203.98
    1,3-propanediol 95.25
    bromobenzene 387.16
    dibromomethane 934.7
    1,1,2,2-tetrachloroethane 1309.75
    2-methyl-cyclohexyl acetate 302.63
    tetrabutyl urea 153.1
    diisobutyl methanol 100.81
    2-phenylethanol 169.25
    styrene 199.68
    dioctyl adipate 212.78
    dimethyl sulfate 160.62
    ethyl butyrate 401.85
    methyl lactate 92.87
    butyl lactate 200.08
    diethyl carbonate 205.01
    propanediol butyl ether 169.56
    triethyl orthoformate 278.12
    p-tert-butyltoluene 82.26
    methyl 4-tert-butylbenzoate 259.21
    morpholine 934.14
    tert-butylamine 188.23
    n-dodecanol 42.67
    dimethoxymethane 404.62
    ethylene carbonate 231.43
    cyrene 232.8
    2-ethoxyethyl acetate 458.22
    2-ethylhexyl acetate 327.24
    1,2,4-trichlorobenzene 381.78
    4-methylpyridine 539.06
    dibutyl ether 293.5
    2,6-dimethyl-4-heptanol 100.81
    DEF 592.65
    dimethyl isosorbide 530.26
    tetrachloroethylene 747.24
    eugenol 216.93
    triacetin 355.02
    span 80 232.75
    1,4-butanediol 38.53
    1,1-dichloroethane 786.43
    2-methyl-1-pentanol 222.31
    methyl formate 71.91
    2-methyl-1-butanol 228.28
    n-decane 19.55
    butyronitrile 285.09
    3,7-dimethyl-1-octanol 111.7
    1-chlorooctane 102.32
    1-chlorotetradecane 32.84
    n-nonane 19.02
    undecane 12.42
    tert-butylcyclohexane 46.76
    cyclooctane 42.3
    cyclopentanol 239.5
    tetrahydropyran 1148.5
    tert-amyl methyl ether 410.31
    2,5,8-trioxanonane 497.19
    1-hexene 200.82
    2-isopropoxyethanol 272.87
    2,2,2-trifluoroethanol 36.15
    methyl butyrate 572.29

    Scent© AI

1 4

IFRA standard 51

Recommendation
No restriction
Maximum acceptable concentrations in the finished product (%)
Category 1
Products applied to the lips
 No restriction Category 7A
Rinse-off products applied to the hair with some hand contact
 No restriction
Category 2
Products applied to the axillae
 No restriction Category 7B
Leave-on products applied to the hair with some hand contact
 No restriction
Category 3
Products applied to the face/body using fingertips
 No restriction Category 8
Products with significant anogenital exposure
 No restriction
Category 4
Products related to fine fragrance
 No restriction Category 9
Products with body and hand exposure, primarily rinse off
 No restriction
Category 5A
Body lotion products applied to the body using the hands (palms), primarily leave on
 No restriction Category 10A
Household care products with mostly hand contact
 No restriction
Category 5B
Face moisturizer products applied to the face using the hands (palms), primarily leave on
 No restriction Category 10B
Household care products with mostly hand contact, including aerosol/spray products (with potential leave-on skin contact)
 No restriction
Category 5C
Hand cream products applied to the hands using the hands (palms), primarily leave on
 No restriction Category 11A
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure
 No restriction
Category 5D
Baby Creams, baby Oils and baby talc
 No restriction Category 11B
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
 No restriction
Category 6
Products with oral and lip exposure
 No restriction Category 12
Products not intended for direct skin contact, minimal or insignificant transfer to skin
 No restriction

Botanical

Name CAS Botanical Proportion
Genet absolute 1 8023-80-1 Spartium junceum L., fam. Leguminosae (Papilionaceae) 1.53%
Parsley absolute (Egypt) 8000-68-8 Petroselinum crispum (Miller) A.W. Hill (P. sativum Hoffm.), fam. Apiaceae 0.16%
Rosa rugosa Rosa rugosa Thunb., var. plena Regel, fam. Rosaceae 0.01%
Hedychium coronarium flower (Japan) Hedychium coronarium Koenig, fam. Zingiberaceae 0.11%
Narcissus poeticus absolute 8023-75-4 Narcissus poeticus L., fam. Amaryllidaceae 0.1%
Mustard seed (China) 1 8007-40-7 Brassica juncea (L.) Czern. et Coss., fam. Brassicaceae (Crucifereae) 4.51%
Genet absolute 2 8023-80-1 Spartium junceum L., fam. Leguminosae (Papilionaceae) 0.7%
Jasmine (China) 1 8022-96-6 Jasminum officinale var. grandiflorum L., fam. Oleaceae 3.22%
Jasmine absolute (Egypt) 4 8022-96-6 Jasminum officinale var. grandiflorum L., fam. Oleaceae 2.09%
Jasmine azoricum concrete Jasminum azoricum L., fam. Oleaceae 2.4%
Jasmine sambac (France) concrete Jasminum sambac (L.) Aiton, fam. Oleaceae 12.6%
Pelargonium reniforme Pelargonium reniforme Curt., fam. Geraniaceae 0.4%
Anthoxanthum odoratum (Italy) 1a fresh leaf Anthoxanthum odoratum L., fam. Poaceae (Gramineae) 0.4%
Cassie absolute 1a extract 8023-82-3 Acacia farnesiana (L.) Willd., fam. Mimosaceae (Leguminosae) 0.5%
Croton jimenezii (Costa Rica) Croton jimenezii Standl. et Valerio, fam. Euphorbiaceae 0.2%